Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
  • D06P1/651—Compounds without nitrogen
  • D06P1/65106—Oxygen-containing compounds
  • D06P1/65118—Compounds containing hydroxyl groups
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/916—Natural fiber dyeing
  • Y10S8/917—Wool or silk
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/924—Polyamide fiber

Definitions

• This invention relates to the dyeing of natural proteinaceous and synthetic polyamide fibers. In particular it is directed to the dyeing of silk, wool and nylon.
• the compounds useful as dye assistants in accordance with the present invention are selected from compounds having the formula:
• one X is hydroxy and the second X is hydrogen or methyl wherein each Y and Z are independently selected from the group consisting of hydrogen and methyl provided that a maximum of one X and Z is methyl and a maximum of one Y is methyl.
• a particularly useful compound is dicyclopentyl alcohol prepared as described by Bruson and Reiner JACS 67 p. 723,
• H Hg H HO H- H a boiling point of about 117 C. at 9 mm.
• Hg a refractive index of about N 1.5262 and an infrared spectrum having strong bands at about 9.4, 10.1, 12.7 and 14.4 microns. Further elucidation of the structure of this compound is discussed by Bartlett and Schneider, JACS 68 6, 1946.
• Another compound useful in the present invention is 3a,4,5,6,7,7a-hexahydro-4,7methanoindan-5-ol.
• This compound can be prepared by the hydrogenation of dicyclopentyl alcohol such as is described in US. Pat. No. 3,062,782, issued Nov. 6, 1962. This compound hereinafter will be referred to as hydrogenated dicyclopentyl alcohol.”
• the new dye assistants of the present invention are particularly useful in the dyeing of natural and synthetic fibers utilizing dyestuffs normally termed acid dyes."
• acid dyes encompasses three types of dyestuffs, i.e., the simple acid dyes, mordant acid dyes and premetalized acid dyes.
• the simple acid dyes fall into various chemical types such as nitro, as exemplified by C1 Acid Yellow 1 (Cl. No. 10316) monoazo, as exemplified by C1 Acid Red 1 (C1. No. 18050); diazo, exemplified by C1 Acid Red 89 (Cl. No. 23910), nitroso, exemplified by C1 Acid Green 1 (C1. No. 10020); monoazo, exemplified by C1 Acid Orange 72 (C.l. No. 18740); triphenylmethane, exemplified by C1 Acid Blue 7 (CI. No. 42080); xanthrene, exemplified by C1 Acid Violet 9 (CI. No.
• mordant acid dyes similarly fall into several chemical types, such as anthraquinone, exemplified by C1 Mordant Red 3 (C.I. No. 58005); monoazo, exemplified by C1 Mordant Red 7 (C1. No. 18760); diazo, exemplified by C1 Mordant Brown 1 (Cl No.
• oxazine exemplified by C1 Mordant Violet 50
• xanthene exemplified by C1 Mordant Red 15
• triphenylamine exemplified by C1 Mordant Blue 1 (C1. No. 43830)
• nitroso exemplified by C1 Mordant Green 4
• naphthoquinone exemplified by C1 Mordant Brown 7.
• the premetalized acid dyes are also divided into several types:
• the actual procedures for applying the dyestuffs to the fibers using the present dye assistants are identical to the standard procedures for the dyeing of natural and synthetic proteinaceous and polyamide fibers using standard acid dye formulations.
• the dye composition can be applied by printing, padding or spraying onto the fabric, or by means of an immersion operation.
• the actual process conditions, such as temperature, pH, etc., are substantially the same as that employed in the art for currently favored systems.
• the dye composition can contain other additives normally used in dyeing with acid dyes.
• thickeners such as methyl celluloses or natural gums are useful for certain applications.
• Other auxiliary materials can also be used such as sodium sulfate, ammonium sulfate, ammonium acetate, ammonium phosphate, methyl and ethyl lactate, methyl and ethyl tartrate, formic acid, acetic acid, hydrochloric acid, sulfuric acid, etc.
• compositions of the present invention contemplate a dye preparation containing as essential components an acid dyestuff useful in the dyeing of synthetic and natural fibers, including silk, wool and nylon, and the prescribed alcohols as an essential dye assistant.
• These compositions can have as optional additional components the aforedescribed additives, such as the thickeners, surfactants, and pH control agents. These additives are often used but the specific ones to be used and their amount can vary with the application.
• the essential dye assistant should be present in an amount of between about 0.25 and about 20 weight percent of the dye composition preferably between about 0.1 and about 10 weight percent of the dye composition.
• Dye Assistant Amount (cc.) Rating Dicyclopcntyl Alcohol 0 0 Dicyclopcntyl Alcohol 0.5 7 Dicyclopentyl Alcohol L0 10 Dicyclopentyl Alcohol L Dicyclopentyl Alcohol 2.0 l0 Benzyl Alcohol 0 0 Benzyl Alcohol 0.5 l Benzyl Alcohol L0 2 Benzyl Alcohol L5 4 Benzyl Alcohol 2.0 6
• the depth of shade of the nylon dyed using dicyclopentyl alcohol constituted a substantial improvement over the depth of shade of the nylon dyed using benzyl alcohol as the dye assistant.
• the nylon dyed using the highest level of benzyl alcohol did not give a dye shade as deep as did the lowest level of dicyclopentyl alcohol (0.5 cc.)
• the dye shade attained by the use of 2.0 cc. of dicyclopentyl alcohol was much deeper than that attained with the use of the same amount of benzyl alcohol.
• Dye pastes were prepared according to the foregoing example, but using Supralan Yellow NR (C.l. No. 18690) as the dye. These pastes were padded onto knitted nylon 6 fiber and pressed to achieve 100 percent add-on as previously described. After steaming, soaping, washing and drying the depth of color of the swatches was rated in a manner similar to the previous example. The following observations were made:
• Dye Assistant Amount (cc.) Rating Dicyclopentyl Alcohol 0 0 Dicyclopentyl Alcohol 0.5 9 Dicyclopentyl Alcohol L0 10 Dicyclopcntyl Alcohol L5 10 Dicyclcpentyl Alcohol 2.0 [0 Benzyl Alcohol 0 0 Bcnzyl Alcohol 0.5 l Benzyl Alcohol I .0 4 Bcnzyl Alcohol L5 8 Benlyl Alcohol 2.0 It) EXAMPLE 3 Dye pastes were prepared according to the following formulations:
• Dyc Assistant Amount Rating Cihaphasol AS 0.5 cc. 0 Cihaphasol AS 2.0 cc. 0 thiodiglyeol 3 c.c. urea 5 g. I Z-cthoxy ethanol 3 cc. urea 5 g. 2 thiourea 5% thiodiglycol 5% Z-hutoxy ethanol 5% 4 benzyl alcohol 2% 4 benzyl alcohol 3% 5 benzyl alcohol 4% 7 dicyclopentyl alcohol I% I0 Additional experiments were performed with other dyes, including Capracyl Orange and Irgalan Red 2 BL. Each of these experiments verified the conclusions that dicyclopentyl alcohol provides excellent depth of shade and levelling, generally superior to that obtained with commonly used dyeing assistants.
• EXAMPLE 4 In order to make certain that the emulsifier is not critical to the performance of the present dyeing assistants, various emulsifiers were utilized in a series of experiments. Since emulsifiers applicable to acid dyeing procedures are generally classified as being anionic or nonionic examples of each classification were used at various levels based on the weight of dicyclopentyl alcohol. Also certain combinations of emulsifiers were used as follows:
• Tile Aim eniul sifiers are rflii amass Chemical lndustries and are polyoxyethylene derivatives and blends with alkyl aryl sulfonates.
• Span 20 is a product of the Atlas Chemical Industries and is Sorbiton monolaurate.
• TRYLOX CO-40 is a product of Trylon Chemical Industries. Inc. and is an ethoxylated caster oil.
• TRYDET 3300? is a product of Trylon Chemical Industries, Inc. and is polyoxyethylene derivatives of fatty acid.
• the present composition can contain thickeners. Thickeners commonly used in preparing pastes with acid dyes are useful in the present compositions in the normal quantities. In order to substantiate this, additional mixtures within the present composition were prepared using a polysaccharide gum, sold under the trademark KELZAN, a trademark of Kelco Co., and compared with a similar composition prepared using as a thickener Polygum 260, a trademark of Polymer Industries, lnc., for sodium alginate.
• EXAMPLE 5 Using Irgalan Green 3 GL as the dye pastes were prepared as described in example Swatches of nylon 6 were dyed and processed in accordance with the methods described in this example. Dicyclopentyl alcohol and benzyl alcohol were used alternately as the dye assistants. The rating were determined as in the previous examples with the following results:
• the amount of thickener used in dye pastes will vary, de pending on the type of dye, the method of application, and the construction of the fabric to be dyed. Pastes used for screen printing will usually be thicker than those used for roller work. Heavy staple fabrics require a thinner paste than would be employed in printing sheer, filament constructions. Normally the thickener would be present in concentrations from about 0.25 percent to about 2 percent of the weight of the total dye paste.
• a dye composition which comprises an acid dyestuff and a dye assistant selected from Z H IY H Z H Y H H H H V Y Y i H and 7& H X' Y X Y H H H wherein one X is hydroxy and the second X is hydrogen or methyl, wherein each Y and Z are independently selected from the group consisting of hydrogen and methyl provided that a maximum of one X and Z is methyl and a maximum of one Y is methyl.
• composition of claim 1 wherein the dye assistant is H H, H
• H0 H- H having a boiling point of about l 17 C. at 9 mm. Hg, 11 refractive index of about N 1.5262 and an infrared spectrum having strong bands at about 9.4, l0.1, 12.7 and 14.4 microns.
• composition of claim 1 wherein the dye assistant is 3a,4,5,6,7,7a-hexahydro-4,7-methanoindan-5-ol.
• composition of claim I wherein the dye assistant is present in a quantity between about 0.25 and about 20 weight percent of the composition.

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Cited By (3)

Citations (2)

• 1970
  • 1970-08-10 US US62687A patent/US3634016A/en not_active Expired - Lifetime
• 1971
  • 1971-07-26 CA CA119,092A patent/CA964008A/en not_active Expired
  • 1971-07-28 AU AU31735/71A patent/AU445669B2/en not_active Expired
  • 1971-08-01 IL IL37417A patent/IL37417A/xx unknown
  • 1971-08-06 DE DE19712139443 patent/DE2139443A1/de active Pending
  • 1971-08-06 NL NL7110904A patent/NL7110904A/xx unknown
  • 1971-08-09 GB GB3725371A patent/GB1327128A/en not_active Expired
  • 1971-08-10 CH CH1174671A patent/CH579177B5/xx not_active IP Right Cessation
  • 1971-08-10 BE BE771135A patent/BE771135A/fr not_active IP Right Cessation
  • 1971-08-10 CH CH1174671D patent/CH1174671A4/xx unknown
  • 1971-08-10 FR FR7129232A patent/FR2104185A5/fr not_active Expired

Patent Citations (2)

Non-Patent Citations (2)

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